Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane

Трофимов, Б. А.; Михалева, А. И.; Иванов, А. В.; Shcherbakova, V. S.; Ushakov, Igor А.

doi:10.1016/j.tet.2014.11.031

Cited by 25 publications

(10 citation statements)

References 50 publications

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“…Therefore, this convenient reaction was used for the generation of the cyclic pyrrole derivatives. By adaptation of the known literature conversion of cyclohexanone ( 7 a ) into the corresponding cyclic 2,3‐alkylpyrrole 8 a , the five mutasynthons 8 a – e of varying ring sizes could be synthesized by starting from cyclic ketones 7 a – e and 1,2‐dichloroethane (Scheme ) . The common moderate yields for this type of reaction were achieved for all cyclic ketones, except for the five‐membered ring analogue 7 b .…”

Section: Resultsmentioning

confidence: 99%

Preparation of Cyclic Prodiginines by Mutasynthesis in Pseudomonas putida KT2440

et al. 2018

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Prodiginines are a group of naturally occurring pyrrole alkaloids produced by various microorganisms and known for their broad biological activities. The production of nature-inspired cyclic prodiginines was enabled by combining organic synthesis with a mutasynthesis approach based on the GRAS (generally recognized as safe) certified host strain Pseudomonas putida KT2440. The newly prepared prodiginines exerted antimicrobial effects against relevant alternative biotechnological microbial hosts whereas P. putida itself exhibited remarkable tolerance against all tested prodiginines, thus corroborating the bacterium's exceptional suitability as a mutasynthesis host for the production of these cytotoxic secondary metabolites. Moreover, the produced cyclic prodiginines proved to be autophagy modulators in human breast cancer cells. One promising cyclic prodiginine derivative stood out, being twice as potent as prodigiosin, the most prominent member of the prodiginine family, and its synthetic derivative obatoclax mesylate.

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Section: Resultsmentioning

confidence: 99%

Preparation of Cyclic Prodiginines by Mutasynthesis in Pseudomonas putida KT2440

et al. 2018

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“…Trofimov showed that ketones could be converted into pyrroles 123 in a one-pot procedure upon treatment with hydroxylamine hydrochloride and KOH, followed by addition of 1,2-dichloroethane (Scheme 13). 64 It is proposed that ketoxime 122 is the putative intermediate in this reaction, which undergoes nucleophilic substitution with 1,2dichloroethane to form O-(2-chloroethyl) ketoxime 124. The ensuing elimination of chloride to N-vinylketoxime 125 then enables 3,3-sigmatropic rearrangement to iminoaldehyde 126; intramolecular condensation then produces the pyrrole core.…”

Section: Ketonesmentioning

confidence: 99%

Recent Advancements in Pyrrole Synthesis

Philkhana¹,

Badmus²,

Reis³

et al. 2021

Synthesis

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This review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle that can be found in numerous compounds of biological and material significance. Given its vast importance, pyrrole continues to be an attractive target for the development of new synthetic reactions. The contents of this article are organized by the starting materials, which can be broadly classified into four different types: substrates bearing π-systems, substrates bearing carbonyl and other polar groups, and substrates bearing heterocyclic motifs. Brief discussions on plausible reaction mechanisms for most transformations are also presented.1 Introduction2 From π-Systems2.1 Alkenes2.2 1,6-Dienes2.3 Allenes2.4 Alkynes2.5 Propargylic Groups2.6 Homopropargylic Amines3 From Carbonyl Compounds3.1 Aldehydes3.2 Ketones3.3 Cyanides and Isocyanides3.4 Formamides3.5 β-Enamines3.6 Dicarbonyl Compounds4 From Polar Compounds4.1 Aminols4.2 Diols4.3 Organonitro Compounds5 From Heterocycles5.1 Münchnones5.2 Isoxazoles5.3 Carbohydrates5.4 trans-4-Hydroxy-l-prolines5.5 Pyrrolines6 Summary

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“…1 H NMR (600 MHz, DMSO-d 6 ): δ = 9.57 (s, 1 H), 7.83 (s, 1 H), 7.61 (s, 1 H), 7.22 (d, J = 8.4 Hz, 2 H), 7.07 (d, J = 8.4 Hz, 2 H), 3.80 (s, 3 H), 3.46 (d, J = 12.0 Hz, 1 H), 2.62 (d, J = 11.4 Hz, 1 H), 2.35 (td, J = 13.2, 6.0 Hz, 1 H), 1.80 (d, J = 11.4 Hz, 1 H), 1.58 (d, J = 13.2 Hz, 1 H), 1.54 (s, 6 H), 1.47-1.41 (m, 1 H), 1.05-0.98 (m, 1 H), 0.89 (t, J = 11.4 Hz, 1 H). 13 C NMR (150 MHz, DMSO-d 6 ): δ = 171. 70, 163.61, 159.24, 130.69, 121.50, 120.15, 114.35, 99.14, 86.89, 71.02, 70.97, 55.19, 27.51, 27.26, 22.27 3380, 3234, 2932, 1677, 1605, 1556, 1481, 1450, 1256, 1076, 938, 786 cm -1 .…”

Section: Acknowledgmentmentioning

confidence: 99%

“…Notably, Trofimov and co-workers described a one-pot strategy for constructing tetrahydroindoles from cyclohexanones, hydroxylamine hydrochloride, and 1,2-dichloroethane in a KOH/DMSO system. 13 Despite the synthetic efficiency of these methods, their expensive precursors and laborious operations limited the regioselectivity and functional diversity of the resulting tetrahydroindoles. Therefore, the development of new and efficient methods for the construction of tetrahydroindole rings from easily available reagents under mild conditions with more flexible substitution patterns remains a desirable objective.…”

mentioning

confidence: 99%

Four-Component Reaction of Substituted β-Nitrostyrenes, Cyclohexanones, Activated Methylene Compounds, and Ammonium Acetate: Efficient Strategy for Construction of Tetrahydroindole Skeletons

Xue

Wang

et al. 2016

Synlett

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An efficient one-pot four-component reaction was developed for the synthesis of two different stereochemical classes of substituted 2-aminotetrahydroindoles from substituted β-nitrostyrenes, cyclohexanones, ammonium acetate, and activated methylene compounds, such as Meldrum's acid, 4-hydroxycoumarin, cyclohexanediones, cyclopentane-1,3-dione, or alkyl cyanoacetates. Both electrondonating and electron-withdrawing groups are tolerated in the aryl ring of the β-nitrostyrene. The reaction utilizes the triethylamine-promoted formation of new C-C and C-N bonds, and simultaneous aromatization in a domino fashion.

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Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane

Cited by 25 publications

References 50 publications

Preparation of Cyclic Prodiginines by Mutasynthesis in Pseudomonas putida KT2440

Preparation of Cyclic Prodiginines by Mutasynthesis in Pseudomonas putida KT2440

Recent Advancements in Pyrrole Synthesis

Four-Component Reaction of Substituted β-Nitrostyrenes, Cyclohexanones, Activated Methylene Compounds, and Ammonium Acetate: Efficient Strategy for Construction of Tetrahydroindole Skeletons

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